US20040175352A1 - Microbicidal compositions including an ionene polymer and 2,4,4-trichloro-2-hydroxydiphenyl ether, and methods of using the same - Google Patents
Microbicidal compositions including an ionene polymer and 2,4,4-trichloro-2-hydroxydiphenyl ether, and methods of using the same Download PDFInfo
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- US20040175352A1 US20040175352A1 US10/383,121 US38312103A US2004175352A1 US 20040175352 A1 US20040175352 A1 US 20040175352A1 US 38312103 A US38312103 A US 38312103A US 2004175352 A1 US2004175352 A1 US 2004175352A1
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- 0 [1*][N+]([2*])(*C)B[N+]([3*])([4*])C Chemical compound [1*][N+]([2*])(*C)B[N+]([3*])([4*])C 0.000 description 6
Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/74—Synthetic polymeric materials
- A61K31/765—Polymers containing oxygen
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/02—Local antiseptics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Definitions
- Many industrial materials and media when wet or subjected to treatment in water are susceptible to bacterial, fungal, and/or algal deterioration or degradation.
- These industrial materials and media include, but are not limited to, for example, wood pulp, wood chips, lumber, adhesives, coatings, animal hides, paper mill liquors, pharmaceutical formulations, cosmetic formulations, toiletry formulations, geological drilling lubricants, petrochemicals, agrochemical compositions, paints, leathers, wood, metalworking fluids, cooling water, recreational water, influent plant water, waste water, pasteurizers, retort cookers, tanning liquors or solutions, starch, proteinaceous materials, acrylic latex paint emulsions, and textiles.
- Ionene polymers i.e., cationic polymers containing quarternary nitrogens in the polymer backbone, are one group of biocides used in controlling bacteria and algae in various aqueous systems. Ionene polymers have a variety of uses in aqueous systems such as, for example, microbicides, bactericides, and algicides, as well as controlling and even preventing biofilm and slime formation. Illustrative examples of these polymers, their uses and preparation are described in U.S. Pat. Nos.
- halogenated diphenyl ether including triclosan
- triclosan tends to be ineffective against certain microbes at relatively low concentrations.
- low concentrations of triclosan tend to be ineffective against certain fungi and some common troublesome industrial bacteria such as Pseudomonas sp.
- Systems or products requiring high concentrations of triclosan tend to be expensive or uneconomical, and limit its use in a number of applications.
- microbicidal composition capable of controlling the growth of at least one microorganism, for example, fungi, bacteria, algae, and mixtures thereof, over prolonged periods of time. It is an additional feature of this invention to provide such compositions which are economical to use. Methods of controlling the growth of at least one microorganism are also features of this invention.
- compositions and processes useful for controlling the growth of one or more microorganisms are described.
- Compositions and methods for preventing damage during storage caused by microorganisms, such as bacteria, fungi, algae, and mixtures thereof, are described.
- the compositions include an ionene polymer and a halogenated diphenyl ether, 2,4,4-trichloro-2-hydroxydiphenylether, also known as triclosan.
- the present invention provides a composition comprising an ionene polymer and triclosan, where the components are present in a combined amount synergistically effective to control the growth of at least one microorganism.
- the present invention provides a method for controlling the growth of at least one microorganism in or on a product, material, or medium susceptible to attack by the microorganism.
- This method includes the step of adding to the product, material, or medium a composition of the present invention in an amount synergistically effective to control the growth of the microorganism.
- the synergistically effective amount varies in accordance with the product, material, or medium to be treated and can, for a particular application, be routinely determined by one skilled in the art in view of the disclosure provided herein.
- the present invention also embodies the separate addition of an ionene polymer and triclosan to products, materials, or media.
- the components are individually added to the products, materials, or media so that the final amount of each component present at the time of use is that amount synergistically effective to control the growth of at least one microorganism.
- compositions of the present invention are useful in preserving or controlling the growth of at least one microorganism in various types of industrial products, media, or materials susceptible to attack by microorganisms.
- Such media or materials include, but are not limited to, for example, dyes, pastes, lumber, leathers, textiles, pulp, wood chips, tanning liquor, paper mill liquor, polymer emulsions, paints, paper and other coating and sizing agents, metalworking fluids, geological drilling lubricants, petrochemicals, cooling water systems, recreational water, influent plant water, waste water, pasteurizers, retort cookers, pharmaceutical formulations, cosmetic formulations, and toiletry formulations.
- composition can also be useful in agrochemical formulations for the purpose of protecting seeds or crops against microbial spoilage.
- the present invention provides a composition to control the growth of at least one microorganism comprising a mixture of an ionene polymer and triclosan, wherein the components are present in a combined amount synergistically effective to control the growth of at least one microorganism.
- the composition preferably provides superior microbicidal activity at low concentrations against a wide range of microorganisms.
- compositions of the present invention can be used in a method for controlling the growth of at least one microorganism in or on a product, material, or medium susceptible to attack by the microorganism.
- This method includes the step of adding to the product, material, or medium a composition of the present invention, where the components of the composition are present in synergistically effective amounts to control the growth of the microorganism.
- synergistically effective amount varies in accordance with the material or medium to be treated and can, for a particular application, be routinely determined by one skilled in the art in view of this disclosure.
- the ionene polymer and a halogenated diphenyl ether for example, trioclosan
- these components are individually added so that the final amount of the mixture of ionene polymer and triclosan at the time of use is that amount synergistically effective to control the growth of at least one microorganism.
- compositions of the present invention are useful in preserving various type of industrial products, media, or materials susceptible to attack by at least one microorganism.
- the compositions of the present invention are also useful in agrochemical formulations for the purpose of protecting seeds or crops against microbial spoilage. These methods of preserving and protecting are accomplished by adding the composition of the present invention to the products, media, or materials in an amount synergistically effective to preserve the products, media, or materials from attack by at least one microorganism or to effectively protect the seeds or crops against microbial spoilage.
- controlling or inhibiting the growth of at least one microorganism includes the reduction and/or the prevention of such growth.
- controlling i.e., preventing
- the growth of the microorganism is inhibited. In other words, there is no growth or essentially no growth of the microorganism.
- Controlling the growth of at least one microorganism maintains the microorganism population at a desired level, reduces the population to a desired level (even to undetectable limits, e.g., zero population), and/or inhibits the growth of the microorganism.
- the products, material, or media susceptible to attack by the at least one microorganism are preserved from this attack and the resulting spoilage and other detrimental effects caused by the microorganism.
- controlling the growth of at least one microorganism also includes biostatically reducing and/or maintaining a low level of at least one microorganism such that the attack by the microorganism and any resulting spoilage or other detrimental effects are mitigated, i.e., the microorganism growth rate or microorganism attack rate is slowed down and/or eliminated.
- An additive effect has no economic advantage over the individual components.
- the antagonistic effect would produce a negative impact. Only a synergistic effect, which is less likely than either an additive or antagonistic effect, would produce a positive effect and therefore possess economic advantages.
- compositions combining an ionene polymer and a halogenated diphenyl ether, for example, triclosan demonstrate unexpected synergistic effects compared to the respective components alone.
- these compositions achieve superior, i.e. greater than additive, microbicidal activity, even at low concentrations, against a wide variety of microorganisms.
- microorganisms include fungi, bacteria, algae, and mixtures thereof, such as, but not limited to, for example, Trichoderma viride, Aspergillus niger, Pseudomonas aeruginosa, Klebsiella pneumoniae , and Chlorella sp.
- the compositions of the present invention have a low toxicity.
- Ionene polymers may be classified according to the repeating unit found in the polymer. This repeating unit results from reactants used to make the ionene polymer.
- a first type of ionene polymer that can be used in the present invention comprises the repeating unit of formula (I):
- R 1 , R 2 , R 3 , and R 4 can be identical or different, and are selected from hydrogen, C 1 -C 20 alkyl, or benzyl.
- Each C 1 -C 20 alkyl can be unsubstituted or substituted, for instance, optionally substituted with at least one hydroxyl group.
- Each benzyl can also be unsubstituted or substituted, for instance, optionally substituted on the benzene moiety with at least one C 1 -C 20 alkyl group.
- R 1 , R 2 , R 3 , and R 4 are all methyl or ethyl.
- the group “A” is a divalent radical selected from C 1 -C 10 alkyl, C 2 -C 10 alkenyl C 2 -C 10 alkynyl, C 1 -C 10 hydroxyalkyl, symmetric or asymmetric di-C 1 -C 10 -alkylether, aryl, aryl-C 1 -C 10 -alkyl, or C 1 -C 10 -alkylaryl-C 1 -C10-alkyl.
- the group “A” can be unsubstituted or substituted.
- A is C 1 -C 5 alkyl, C 2 -C 5 alkenyl, C 2 -C 5 hydroxyalkyl, or symmetric di-C 2 -C 5 -alkylether. Most preferably “A” is propylene, 2-hydroxypropylene, or diethylene ether.
- the group “B” is a divalent radical, which can be the same as the group “A,” and is selected from C 1 -C 10 alkyl, C 2 -C 10 alkenyl, C 2 -C 10 alkynyl, C 1 -C 10 hydroxyalkyl, symmetric or asymmetric di-C 1 -C 10 -alkylether, aryl, aryl-C 1 -C 10 -alkyl, or C 1 -C 10 -alkylaryl-C 1 -C 10 -alkyl.
- the group “B” can be unsubstituted or substituted.
- B is C 1 -C 5 alkyl, C 2 -C 5 alkenyl, C 2 -C 5 hydroxyalkyl, aryl, aryl-C 1 -C 5 -alkyl, or C 1 -C 5 -alkylaryl-C 1 -C 5 -alkyl.
- B is ethylene, propylene, butylene, or hexamethylene.
- the counter ion, X 2 ⁇ is a divalent counter ion, two monovalent counter ions, or a fraction of a polyvalent counter ion sufficient to balance the cationic charge in the repeating unit which forms the ionene polymer backbone.
- X 2 ⁇ is two monovalent anions selected from a halide anion and a trihalide anion and more preferably, chloride or bromide. Ionene polymers having trihalide counter ions are described, for example, in U.S. Pat. No. 3,778,476, the disclosure of which is incorporated herein in its entirety by reference.
- Ionene polymers having the repeating unit of formula (I) may be prepared by any of the methods known to one of ordinary skill in the art. One such method is to react a diamine of the formula R 1 R 2 N—B—NR 3 R 4 with a dihalide of the formula X—A—X, wherein the substituents R 1 , R 2 , R 3 , R 4 , A, X, and B have the same meanings as in formula (I). Ionene polymers having this repeating unit and methods for their preparation are described, for example, in U.S. Pat. Nos.
- a second type of ionene polymer that can be used in the present invention comprises the repeating unit of formula (II):
- X ⁇ is a monovalent counter ion, one-half of a divalent counter ion, or a fraction of a polyvalent counter ion sufficient to balance the cationic charge of the repeating unit which forms the ionene polymer.
- X ⁇ can be, for example, a halide or trihalide anion, and is preferably chloride or bromide.
- Ionene polymers having the repeating unit of formula (II) may also be prepared by any of the known methods.
- One method is to react an amine of the formula R 1 R 2 N with a haloepoxide such as epichlorohydrin or (chloromethyl) oxirane, wherein R 1 and R 2 have the same meanings as in formula (I).
- Ionene polymers having the repeating unit of formula (II) are, for example, described in U.S. Pat. Nos. 4,111,679 and 5.051,124, the disclosures of which are incorporated herein in their entireties by reference. The biological activity of ionene polymers having the repeating unit of formula (II) is also described in these patents.
- a third type of ionene polymer that can be used in the present invention comprises a repeating unit of formula (III):
- n and p are integers and independently vary from 2 to 12; each R′ is independently hydrogen or a lower alkyl group (e.g., C 1 -C 12 alkyl) wherein the alkyl group is unsubstituted or substituted; X 2 ⁇ is a divalent counter ion, two monovalent counter ions, or a fraction of a polyvalent counter ion sufficient to balance the cationic charge in the group R; and X ⁇ is a monovalent counter ion, one-half of a divalent counter ion, or a fraction of a polyvalent counter ion sufficient to balance the cationic charge in the group B′.
- each R′ is independently hydrogen or a lower alkyl group (e.g., C 1 -C 12 alkyl) wherein the alkyl group is unsubstituted or substituted
- X 2 ⁇ is a divalent counter ion, two monovalent counter ions, or a fraction of a polyvalent counter ion sufficient to balance
- R′ is hydrogen or a C 1 -C 4 alkyl; n is 2-6 and p is 2-6. Most preferably, R′ is hydrogen or methyl, n is 3 and p is 2.
- Preferred counter ions, X 2 ⁇ and X ⁇ are the same as those discussed above with respect to formulae (I) and (II).
- the polymers of formula (III) may be derived from bis(dialkylaminoalkyl) ureas, which are also known as urea diamines, by known methods. Ionene polymers of formula (III), methods of their preparation, and their biological activities are, for example, described in U.S. Pat. No. 4,506,081; the disclosure of which is incorporated herein in its entirety by reference.
- Ionene polymers comprising the repeating units of formulae (I), (II), and (III) may also be cross-linked with primary, secondary, or other polyfunctional amines using means known in the art. Ionene polymers can be cross-linked either through the quaternary nitrogen atom, or through another functional group attached to the polymer backbone or to a side chain.
- Cross-linked ionene polymers prepared using cross-linking coreactants, are disclosed in U.S. Pat. No. 3,738,945 and U.S. Pat. No. RE 28,808, the disclosures of each of which are incorporated herein in their entireties by reference.
- U.S. Pat. No. RE 28,808 describes the cross-linking of ionene polymers prepared by the reaction of dimethylamine and epichlorohydrin.
- the cross-linking co-reactants listed are ammonia, primary amines, alkylenediamines, polyglycolamines, piperazines, heteroaromatic diamines, and aromatic diamines.
- the ionene polymers comprising the repeating units of formulae (I), (II), or (III) may also be capped, i.e., have a specific end group. Capping may be achieved by any means known in the art. For example, an excess of one of the reactants used to make the ionene polymer can be employed to provide a capping group. Alternatively, a calculated quantity of a monofunctional tertiary amine or monofunctional substituted or unsubstituted alkyl halide can be reacted with an ionene polymer to obtain a capped ionene polymer. Ionene polymers can be capped at one or both ends. Capped ionene polymers and their microbicidal properties are described in U.S. Pat. Nos. 3,931,319 and 5,093,078. The disclosures of each of these patents are incorporated herein in their entireties by reference.
- the specific ionene polymer employed is preferably selected based on the compatibility with the medium of intended use. Compatibility is determined by criteria such as solubility in the fluid system and lack of reactivity with the fluid or material or media in question. The compatibility is readily determined by one of ordinary skill by adding the ionene polymer to the material or media to be used. When used in a fluid system, it is preferable that the ionene polymer be freely soluble in the particular fluid, resulting in a uniform solution or dispersion.
- a particularly preferred ionene polymer having a repeating unit of formula (I) is poly(oxyethylene(dimethyliminio)ethylene(di-methyliminio)ethylene dichloride).
- R 1 , R 2 , R 3 , and R 4 are each methyl, A is —CH 2 CH 2 OCH 2 CH 2 —, B is —CH 2 CH 2 —, and X 2 ⁇ is 2Cl ⁇ , and the average molecular weight is 1,000-5,000.
- This ionene polymer is available from Buckman Laboratories, Inc. of Memphis, Tenn.
- Busan® 77 product a 60% aqueous dispersion of the polymer
- WSCP® product a 60% aqueous dispersion of the polymer.
- Busan® 77 and WSCP® products are biocides used primarily in aqueous systems, including metalworking fluids for microorganism control.
- Another particularly preferred ionene polymer having a repeating unit of formula (I), also available from Buckman Laboratories, Inc. as Busan® 79 product, or WSCP II product is the ionene polymer where R 1 , R 2 , R 3 , and R 4 are each methyl, A is —CH 2 CH(OH)CH 2 —, B is —CH 2 CH 2 —, and X 2 ⁇ is 2Cl ⁇ .
- This ionene polymer is a reaction product of N,N,N′,N′-tetramethyl-1,2-ethanediamine, with (chloromethyl)oxirane, and has a 1,000-5,000 average molecular weight.
- the polymer product Busan® 79 or WSCP® II product is a 60% aqueous solution of the polymer.
- Preferred ionene polymers having the repeating unit of formula (II) are those where R 1 and R 2 are each methyl, A is —CH 2 CH(OH)CH 2 —, and X ⁇ is Cl ⁇ .
- Busan® 1055 product is a 50% aqueous dispersion of such an ionene polymer obtained as a reaction product of dimethylamine with (chloromethyl)oxirane having a 2,000-10,000 average molecular weight.
- Busan 1055 is also known as APCA.
- Busan® 1157 product is a 50% aqueous dispersion of the ionene polymer having the repeating unit of formula (II), obtained as a reaction product of dimethylamine with epichlorohydrin, cross-linked with ethylenediamine, where R 1 and R 2 are each methyl, A is —CH 2 CH(OH)CH 2 — and X ⁇ is Cl ⁇ .
- This ionene polymer has a 100,000-500,000 average molecular weight.
- Busan® 1155 product is a 50% aqueous dispersion of an ionene polymer having the repeating unit of formula (II), where R 1 and R2 are each methyl, A is —CH 2 CH(OH)CH 2 —, X ⁇ is Cl ⁇ and the ionene polymer is cross-linked with ammonia.
- This ionene polymer has a molecular weight of approximately 100,000-500,000.
- Busan® 1099 product or Bubond® 65 product is a 25% aqueous dispersion of a cross-linked ionene polymer having repeating units of formula (II), where R 1 and R 2 are each methyl, A is —CH 2 CH(OH)CH 2 —, X ⁇ is Cl ⁇ , the cross-linking agent is monomethylamine.
- This ionene polymer has a molecular weight of approximately 10,000-100,000.
- Preferred ionene polymers having the repeating unit of formula (III) are those where R is a urea diamine and X 2 ⁇ is 2Cl ⁇ , B′ is CH 2 CH(OH)CH 2 , and X ⁇ is Cl ⁇ .
- BL® 1090 is a 50% aqueous dispersion of the ionene polymer obtained as a reaction product of N,N′-bis-[1-(3-(dimethylamino))-propyl]urea and epichlorohydrin, such an ionene polymer having a 2,000-15,000, preferably 3,000-7,000, average molecular weight.
- Triclosan is commercially available and also easily synthesized from commercially available raw materials.
- a preferred halogenated diphenylether is 2,4,4′-tricloro-2′-hydroxydiphenyl ether, or triclosan.
- components (a) an ionene polymer and (b) triclosan are used in a synergistically effective amounts.
- the weight ratios of (a) to (b) vary depending on the type of microorganisms and product, material, or media to which the composition is applied. In view of the present invention, one skilled in the art can readily determine, without undue experimentation, the appropriate weight ratios for a specific application.
- the ratio of component (a) to component (b) preferably ranges from 1:99 to 99:1, more preferably from 1:30 to 30:1, and most preferably 1:2 to 2:1.
- the composition can be prepared in liquid form by dissolving the composition in water or in an organic solvent, or in dry form by adsorbing onto a suitable vehicle, or compounding into a tablet form.
- the preservative containing the composition of the present invention may be prepared in an emulsion form by emulsifying it in water, or if necessary, by adding a surfactant. Additional chemicals, such as insecticides, may be added to the foregoing preparations depending upon the intended use of the preparation.
- compositions of this invention could vary depending upon the intended use.
- the composition could be applied by spraying or brushing onto the material or product.
- the material or product in question could also be treated by dipping in a suitable formulation of the composition.
- the composition In a liquid or liquid-like medium, the composition could be added into the medium by pouring, or by metering with a suitable device so that a solution or a dispersion of the composition can be produced.
- Mineral salts-glucose medium was used. To prepare the medium, the following ingredients were added to 1 liter of deionized water: 0.7 g of KH 2 PO 4 ; 0.7 g of MgSO 4 .7H 2 O; 1.0 g of HN 4 NO 3 ; 0.005 g of NaCl; 0.002 g of FeSO 4 .7H 2 0; 0.002 g ZnSO 4 .7H 2 O; 0.001 g of MnSO 4 .7H 2 O; 10 g of Glucose. The pH of the medium was adjusted to 6 with 1N NaOH. The medium was distributed in 5 ml amounts in test tubes and autoclaved at 121° C. for 20 minutes.
- the fungus Trichoderma viride or Aspergillus niger , was grown on potato dextrose agar slant for 5 to 10 days and a spore suspension prepared by washing down the spores from the slant into a sterile saline solution. After addition of the biocides in the desired concentrations in the sterile mineral salts-glucose medium, the fungal spore suspension was added. The final spore concentration was approximately 10 6 cfu/ml. The inoculated media was incubated at 25° C. for 7 days.
- Nutrient broth (2.5 g/liter of deionized water) was prepared. This was distributed in 5 ml amounts in test tubes and autoclaved at 121° C. for 20 minutes. After addition of the biocides in the desired concentrations to the nutrient broth, 100 microliters of a 24-hour grown suspension of Pseudomonas aeruginosa or Klebsiella pneumoniae cells of approximately 9.3 ⁇ 10 8 cfu/ml were added and incubated at 30° C. for 24 or 48 hours.
- the medium used for testing the effectiveness of the invention against algae was modified Allen's medium (see Allen, A. A., Simple conditions for growth of unicellular blue-green algae on plates , JOURNAL OF PHYCOLOGY. 4:1-4 (1986)).
- modified Allen's medium the following six individual stock solutions in g/200 ml of deionized water were first prepared: 1.50 g of K 2 HPO 4 ; 1.50 g of MgSO 4 .7H 2 0; 0.80 g Na 2 CO 3 ; 0.5 g CaCl 2 .2H 2 O; 1.16 g Na 2 SiO 3 .9H 2 O; 1.20 g citric acid.
- a micronutrient stock solution was also prepared by adding the following ingredients to 1 liter of deionized water: 0.75 g of Na 2 EDTA; 0.097 g FeCl 3 .6H 2 O; 0.041 g of MnCl 2 .4H 2 O; 0.005 g ZnCl 2 ; 0.002 g CoCl 2 .6H 2 O; 0.004 g Na 2 MoO 4 .2H 2 O.
- the biocides were added to the medium in the desired concentrations. Then one milliliter of a two-week old culture of Chlorella sp. was added and incubated at a temperature of 25° C., and lighting of 180 ft-candle intensity for 3 or 4 weeks.
- QA Concentration of compound A in parts per million, in the mixture, which produced an end point.
- QB Concentration of compound B in parts per million, in the mixture, which produced an end point.
- an effective fungicidal, bactericidal, or algicidal response can be obtained when the synergistic combination is employed in concentrations ranging about 0.01 ppm to 1% (i.e., 10,000 ppm) of the ionene polymer, preferably 0.1 to 5,000 ppm, and most preferably 0.1 ppm to 1000 ppm; and from about 0.01 to 5,000 ppm of triclosan, preferably 0.1 to 3,000 ppm, and most preferably, 0.1 to 1,000 ppm.
- the present invention is quite effective as a antimicrobial agent, and preferably provides synergistic results.
- One of the important aspects of the present invention is the ability to have effectiveness against Pseudomonas sp., especially with relatively low concentrations of triclosan and ionene polymers. It is interesting to note that when triclosan and ionene polymers are used individually, triclosan is ineffective against Pseudomonas sp., and relatively high concentration of ionene polymers are required to control this organism. This is an additional benefit and unexpected benefit of the present invention.
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Priority Applications (10)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/383,121 US20040175352A1 (en) | 2003-03-06 | 2003-03-06 | Microbicidal compositions including an ionene polymer and 2,4,4-trichloro-2-hydroxydiphenyl ether, and methods of using the same |
PCT/US2004/006861 WO2004080176A2 (fr) | 2003-03-06 | 2004-03-05 | Compositions microbicides comprenant un polymere d'ionene et de l'ether de 2,4,4'-trichloro-2'-hydroxydiphenyle, et leurs procedes d'utilisation |
CA002517610A CA2517610A1 (fr) | 2003-03-06 | 2004-03-05 | Compositions microbicides comprenant un polymere d'ionene et de l'ether de 2,4,4'-trichloro-2'-hydroxydiphenyle, et leurs procedes d'utilisation |
AU2004220618A AU2004220618A1 (en) | 2003-03-06 | 2004-03-05 | Microbicidal compositions including an ionene polymer and 2,4,4'-trichloro-2'-hydroxydiphenyl ether, and methods of using the same |
CNA2004800060774A CN1756484A (zh) | 2003-03-06 | 2004-03-05 | 包括阳离子聚合物和2,4,4′-三氯-2′-羟基二苯醚的杀微生物组合物以及使用它的方法 |
BRPI0408673-2A BRPI0408673A (pt) | 2003-03-06 | 2004-03-05 | composições microbicidas incluindo um polìmero inoneno e 2,4,4'-tricloro-2'-hidroxidifenil éter, e métodos para usá-las |
EP04718106A EP1603390A2 (fr) | 2003-03-06 | 2004-03-05 | Compositions microbicides comprenant un polymere d'ionene et de l'ether de 2,4,4'-trichloro-2'-hydroxydiphenyle, et leurs procedes d'utilisation |
JP2006509197A JP2006522121A (ja) | 2003-03-06 | 2004-03-05 | イオネンポリマーと2,4,4’−トリクロロ−2’−ヒドロキシジフェニルエーテルとを含む殺菌性組成物並びにその使用方法 |
MXPA05009475A MXPA05009475A (es) | 2003-03-06 | 2004-03-05 | Composiciones microbicidas que incluyen un polimero de ioneno y eter 2,4,4'-tricloro-2'-hidroxidifenilico, y metodos para usar las mismas. |
ZA200506601A ZA200506601B (en) | 2003-03-06 | 2005-08-18 | Microbicidal compositions including an ionene polymer and 2,4,4'-trichloro-2'-hydroxydiphenyl ether and methods of using the same |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/383,121 US20040175352A1 (en) | 2003-03-06 | 2003-03-06 | Microbicidal compositions including an ionene polymer and 2,4,4-trichloro-2-hydroxydiphenyl ether, and methods of using the same |
Publications (1)
Publication Number | Publication Date |
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US20040175352A1 true US20040175352A1 (en) | 2004-09-09 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US10/383,121 Abandoned US20040175352A1 (en) | 2003-03-06 | 2003-03-06 | Microbicidal compositions including an ionene polymer and 2,4,4-trichloro-2-hydroxydiphenyl ether, and methods of using the same |
Country Status (10)
Country | Link |
---|---|
US (1) | US20040175352A1 (fr) |
EP (1) | EP1603390A2 (fr) |
JP (1) | JP2006522121A (fr) |
CN (1) | CN1756484A (fr) |
AU (1) | AU2004220618A1 (fr) |
BR (1) | BRPI0408673A (fr) |
CA (1) | CA2517610A1 (fr) |
MX (1) | MXPA05009475A (fr) |
WO (1) | WO2004080176A2 (fr) |
ZA (1) | ZA200506601B (fr) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20060169431A1 (en) * | 2005-01-05 | 2006-08-03 | Marks Thomas I | Enhanced efficacy of fungicides in paper and paperboard |
US20080249136A1 (en) * | 2005-10-25 | 2008-10-09 | Ioana Annis | Antimicrobial Composition and Method |
US20100173018A1 (en) * | 2009-01-08 | 2010-07-08 | Buckman Laboratories International, Inc. | Microbicidal Compositions Including Activated Nitrogenous Compound and 1,4-Bis(Bromoacetoxy)-2-Butene, and Methods Of Using The Same |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102005043428A1 (de) * | 2005-09-13 | 2007-03-15 | Lanxess Deutschland Gmbh | Verwendung von Triclosan für den Holzschutz |
BR112017017486B1 (pt) * | 2015-02-19 | 2022-06-28 | Yeditepe Universitesi | Formulação de revestimento para semente |
WO2019071500A1 (fr) * | 2017-10-12 | 2019-04-18 | The Procter & Gamble Company | Composition détergente antimicrobienne de blanchisserie |
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- 2003-03-06 US US10/383,121 patent/US20040175352A1/en not_active Abandoned
-
2004
- 2004-03-05 CN CNA2004800060774A patent/CN1756484A/zh active Pending
- 2004-03-05 WO PCT/US2004/006861 patent/WO2004080176A2/fr active Application Filing
- 2004-03-05 EP EP04718106A patent/EP1603390A2/fr not_active Withdrawn
- 2004-03-05 MX MXPA05009475A patent/MXPA05009475A/es unknown
- 2004-03-05 CA CA002517610A patent/CA2517610A1/fr not_active Abandoned
- 2004-03-05 BR BRPI0408673-2A patent/BRPI0408673A/pt not_active IP Right Cessation
- 2004-03-05 JP JP2006509197A patent/JP2006522121A/ja not_active Withdrawn
- 2004-03-05 AU AU2004220618A patent/AU2004220618A1/en not_active Abandoned
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2005
- 2005-08-18 ZA ZA200506601A patent/ZA200506601B/en unknown
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US3231509A (en) * | 1964-06-11 | 1966-01-25 | Betz Laboratories | Slimicidal composition and method |
US3629477A (en) * | 1966-08-08 | 1971-12-21 | Geigy Chem Corp | Halogenated diphenyether-containing compositions and control of pests therewith |
US3778476A (en) * | 1970-05-11 | 1973-12-11 | California Inst Of Techn | Polymeric organic halogen salts |
US3898336A (en) * | 1970-05-11 | 1975-08-05 | California Inst Of Techn | Insoluble polymeric quaternary trihalogen salt coated substrates |
USRE28808E (en) * | 1972-02-04 | 1976-05-11 | American Cyanamid Company | Polyquaternary flocculants |
US3738945A (en) * | 1972-02-04 | 1973-06-12 | H Panzer | Polyquaternary flocculants |
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US3930877A (en) * | 1973-08-13 | 1976-01-06 | Nalco Chemical Company | Cationic starch and condensates for making the same |
US3874870A (en) * | 1973-12-18 | 1975-04-01 | Mill Master Onyx Corp | Microbiocidal polymeric quarternary ammonium compounds |
US4025627A (en) * | 1973-12-18 | 1977-05-24 | Millmaster Onyx Corporation | Microbiocidal polymeric quaternary ammonium compounds |
US3931319A (en) * | 1974-10-29 | 1976-01-06 | Millmaster Onyx Corporation | Capped polymers |
US4027020A (en) * | 1974-10-29 | 1977-05-31 | Millmaster Onyx Corporation | Randomly terminated capped polymers |
US4010252A (en) * | 1974-12-19 | 1977-03-01 | Colgate-Palmolive Company | Antimicrobial compositions |
US4054542A (en) * | 1975-04-14 | 1977-10-18 | Buckman Laboratories, Inc. | Amine-epichlorohydrin polymeric compositions |
US4089977A (en) * | 1976-11-24 | 1978-05-16 | Kewanee Industries | Polymeric anti-microbial agent |
US4164521A (en) * | 1977-02-07 | 1979-08-14 | American Cyanamid Company | Mixtures of polycationic and polyanionic polymers for scale control |
US4147627A (en) * | 1977-02-07 | 1979-04-03 | American Cyanamid Company | Process for scale control using mixtures of polycationic and polyanionic polymers |
US4098788A (en) * | 1977-06-20 | 1978-07-04 | Bristol-Myers Company | Process for preparing quinazolines |
US4111679A (en) * | 1977-08-17 | 1978-09-05 | Chemed Corporation | Polyquaternary compounds for the control of microbiological growth |
US4166041A (en) * | 1977-12-15 | 1979-08-28 | American Cyanamid Company | Process for magnesium scale control using mixtures of polycationic and polyanionic polymers |
US4104161A (en) * | 1978-04-18 | 1978-08-01 | Nalco Chemical Company | Method for treating aqueous wastes containing at least 1% proteinaceous matter |
US4506081A (en) * | 1982-09-02 | 1985-03-19 | Buckman Laboratories, Inc. | Polymeric quaternary ammonium compounds and their uses |
US4581058A (en) * | 1982-09-02 | 1986-04-08 | Buckman Laboratories, Inc. | Polymeric quaternary ammonium compounds and their uses |
US4606773A (en) * | 1984-12-10 | 1986-08-19 | Nalco Chemical Company | Emulsification of alkenyl succinic anhydride sizing agents |
US4769155A (en) * | 1987-08-19 | 1988-09-06 | Nalco Chemical Company | Turbidity reduction |
US5093078A (en) * | 1989-02-10 | 1992-03-03 | Buckman Laboratories International, Inc. | Novel polymeric quaternary ammonium trihalides and use of polymeric quaternary ammonium trihalides as microbicides, sanitizers and disinfectants |
US5371083A (en) * | 1989-09-27 | 1994-12-06 | Buckman Laboratories International, Inc. | Synergistic combinations of ionenes with hexahydro-1,3,5-tris-(2-hydroxyethyl)-s-triazine in controlling fungal and bacterial growth in synthetic metalworking fluids |
US5051124A (en) * | 1989-10-24 | 1991-09-24 | Buckman Laboratories International, Inc. | Microbicidal compositions of dimethylamine-epichlorohydrin amines |
US5350679A (en) * | 1993-06-14 | 1994-09-27 | Dow Corning Corporation | Repeat insult microbial test method |
US20010016589A1 (en) * | 1995-11-13 | 2001-08-23 | Shanta Modak | Triple antimicrobial composition |
US5843865A (en) * | 1996-02-07 | 1998-12-01 | Buckman Laboratories International, Inc. | Synergistic antimicrobial compositions containing an ionene polymer and a salt of dodecylamine and methods of using the same |
US5776960A (en) * | 1996-10-16 | 1998-07-07 | Buckman Laboratories International, Inc. | Synergistic antimicrobial compositions containing an ionene polymer and a pyrithione salt and methods of using the same |
US5866016A (en) * | 1997-07-01 | 1999-02-02 | Buckman Laboratories International, Inc. | Methods and compositions for controlling biofouling using combinations of an ionene polymer and a salt of dodecylamine |
US6133483A (en) * | 1998-07-30 | 2000-10-17 | Cleary; Thomas F. | Process for the production of 2,4,4'-trichloro-2'-methoxydiphenyl ether |
US6147120A (en) * | 1999-02-16 | 2000-11-14 | Ecolab Inc. | Synergistic antimicrobial skin washing compositions |
US6294589B1 (en) * | 2000-05-12 | 2001-09-25 | Shaw Industries, Inc. | Polyurethane composition containing antimicrobial agents and methods for use therefor |
US20030026833A1 (en) * | 2001-07-10 | 2003-02-06 | Payne Stephen A. | Synergistic antimicrobial textile finish |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20060169431A1 (en) * | 2005-01-05 | 2006-08-03 | Marks Thomas I | Enhanced efficacy of fungicides in paper and paperboard |
US20080249136A1 (en) * | 2005-10-25 | 2008-10-09 | Ioana Annis | Antimicrobial Composition and Method |
US20100173018A1 (en) * | 2009-01-08 | 2010-07-08 | Buckman Laboratories International, Inc. | Microbicidal Compositions Including Activated Nitrogenous Compound and 1,4-Bis(Bromoacetoxy)-2-Butene, and Methods Of Using The Same |
Also Published As
Publication number | Publication date |
---|---|
BRPI0408673A (pt) | 2006-03-28 |
ZA200506601B (en) | 2006-06-28 |
CN1756484A (zh) | 2006-04-05 |
WO2004080176A2 (fr) | 2004-09-23 |
EP1603390A2 (fr) | 2005-12-14 |
CA2517610A1 (fr) | 2004-09-23 |
MXPA05009475A (es) | 2005-11-23 |
WO2004080176A3 (fr) | 2004-12-09 |
AU2004220618A1 (en) | 2004-09-23 |
JP2006522121A (ja) | 2006-09-28 |
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Owner name: BUCKMAN LABORATORIES, INC., TENNESSEE Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:OPPONG, DAVID;VUNK, GRACIELLA H.;FUES, RUSSELL E.;REEL/FRAME:013848/0968 Effective date: 20030206 |
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